Hydrogen Peroxide → 1-Methyl-1-phenylundecyl hydroperoxide

HRID 241465

Reaction equation

HRID 241465 reaction equation
[OH:1][OH:2].C1COCC1.[C:8]1([C:14](Br)([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>FC(F)(F)C([O-])=O.[Ag+].C([O-])(O)=O.[Na+]>[CH3:15][C:14]([O:1][OH:2])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 67084407HCID 67084407, compound

Product 1

HCID 866430191-Methyl-1-phenylundecyl hydroperoxide

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

10.50 g (0.04 mol) of 1-methyl-1-phenylundecyl alcohol was dissolved in 50 ml of dichloromethane, cooled in ice bath, 10.6 ml (12.29 g, 0.08 mol) of trimethylsilyl bromide was added and the mixture stirred for 1 h under protection from moisture. The solution was diluted with 100 ml ether and washed four times with 50 ml water, brine, dried and evaporated to give crude 2-phenyl-2-bromododecane. 35 ml of 2.3 M hydrogen peroxide in THF (0.08 mol) was added to the 2-phenyl-2-dodecyl bromide and the mixture was cooled on ice bath. 8.84 g (0.04 mol) of silver trifluoroacetate was added. 70 ml of conc. NaHCO3 was added and the mixture filtered. The reaction flask and the filter cake was rinsed with diethyl ether. The aqueous phase was separated and the organic phase washed with conc. NaHCO3, 50 ml water, brine, dried and evaporated to give an oil. The oil was purified by flash chromatography using 2:8 ether:pentane as eluent. The yield of 1-methyl-1-phenylundecyl hydroperoxide was 30%.

Workup

  1. temperaturethe mixture was cooled on ice bath
  2. filtrationthe mixture filtered
  3. washThe reaction flask and the filter cake was rinsed with diethyl ether
  4. customThe aqueous phase was separated
  5. washthe organic phase washed with conc. NaHCO3, 50 ml water, brine
  6. customdried
  7. customevaporated
  8. customto give an oil
  9. customThe oil was purified by flash chromatography

Sources & evidence

ORD record
ord-0d011dcd27524acc9b0ac7e4ad0d3f9c
Source dataset
uspto-grants-2014_02
Patent number
US08650742B2

Linked notes

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